Meta-bis anilide derivatives and their utility as herbicides

Abstract

Compounds corresponding to the formula: ##SPC1## In which R 1 and R 2 are, independently, hydrogen, alkyl, alkoxyalkyl, cycloalkyl, pinonyl, ethylcycloalkyl, lower alkenyl, halogenated lower alkyl, benzyl, ethylphenyl, 2,4-dichlorophenoxy-methylene, styryl, furyl, phenyl or substituted phenyl in which the substituents are nitro, halogen, methyl, or methoxy; R 3 and R 4 are, independently, hydrogen or lower alkyl; X and Y are independently oxygen or sulfur; and Z is halogen, nitro, amino, lower alkyl, lower alkoxy or trifluoromethyl and n is an integer having a value from 0 to 4. The above compounds are effective herbicides, particularly for the control of grasses and broadleaf plants with both pre-emergence and post-emergence activity. Representative compounds are: m-propionamidobutyranilide, m-bis-2,2-dimethylvaleranilide, m-isobutyramido trichloroacetanilide, m-isobutyramido-2-ethylbutyranilide, m-t-butylacetamidopropanilide, and 3'-N-ethyl propionamido-propanilide.

What is claimed is: 
     
       1. A method for controlling the growth of vegetation which comprises applying to the area where control of said vegetative growth is desired, a growth controlling amount of a compound having the formula ##SPC4## in which R 1  and R 2  are independently selected from the group consisting of alkyl containing from 1 through about 10 carbon atoms, inclusive, and lower alkenyl.   
     
     
       2. The method according to claim 1 in which R 1  and R 2  are independent alkyl groups. 
     
     
       3. The method according to claim 2 in which R 1  is ethyl and R 2  is n-propyl. 
     
     
       4. The method according to claim 2 in which R 1  is 1,1-dimethylbutyl and R 2  is 1,1-dimethylbutyl. 
     
     
       5. The method according to claim 2 in which R 1  is 1-ethylpropyl and R 2  is isopropyl. 
     
     
       6. The method according to claim 2 in which R 1  is neopentyl and R 2  is ethyl. 
     
     
       7. The method according to claim 2 in which R 1  is neopentyl and R 2  is isopropyl. 
     
     
       8. The method according to claim 2 in which R 1  is tert-butyl and R 2  is neopentyl. 
     
     
       9. The method according to claim 2 in which R 1  is 1,1-dimethylbutyl and R 2  is neopentyl. 
     
     
       10. The method according to claim 2 in which R 1  is sec-butyl and R 2  is ethyl. 
     
     
       11. The method according to claim 2 in which R 1  is sec-butyl and R 2  is sec-butyl. 
     
     
       12. The method according to claim 2 in which R 1  is sec-butyl and R 2  is tert-butyl. 
     
     
       13. The method according to claim 2 in which R 1  is sec-butyl and R 2  is neopentyl. 
     
     
       14. The method according to claim 2 in which R 1  is 1-ethylpropyl and R 2  is ethyl. 
     
     
       15. The method according to claim 2 in which R 1  is 1,1-dimethylbutyl and R 2  is ethyl. 
     
     
       16. The method according to claim 1 in which R 1  is lower alkenyl and R 2  is lower alkenyl. 
     
     
       17. The method according to claim 16 in which R 1  is 2,2-dimethylvinyl and R 2  is 2,2-dimethylvinyl. 
     
     
       18. The method according to claim 1 in which R 1  is lower alkenyl and R 2  is alkyl. 
     
     
       19. The method according to claim 18 in which R 1  is 2,2-dimethylvinyl, R 2  is tert-butyl. 
     
     
       20. The method according to claim 18 in which R 1  is 2,2-dimethylvinyl, R 2  is 1,1-dimethylbutyl. 
     
     
       21. The method according to claim 18 in which R 1  is 2,2-dimethylvinyl, R 2  is ethyl. 
     
     
       22. The method according to claim 18 in which R 1  is vinyl, R 2  is ethyl. 
     
     
       23. A method according to claim 2 in which R 1  is 2,4,4-trimethylpentyl and R 2  is 1,1-dimethylbutyl. 
     
     
       24. A method according to claim 2 in which R 1  is 1-methylbuyl and R 2  is tert-butyl.